2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 67364747, 화합물

HRID 245757노트

반응식

HRID 245757 반응식
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].[Cl:19][C:20]1[CH:21]=[C:22]2[CH:28]=[C:27]([C:29](OC)=[O:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]2[CH:28]=[C:27]([C:29]([NH:5][C:4]3[CH:6]=[CH:7][C:8]([B:10]4[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]4)=[CH:9][C:3]=3[O:2][CH3:1])=[O:30])[N:26]([CH3:33])[C:23]2=[N:24][CH:25]=1

참가 물질

4

반응물 2

HCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67363339HCID 67363339, 화합물

생성물 1

HCID 67364747HCID 67364747, 화합물수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.073 g, 8.32 mmol) in tetrahydrofuran (dry) (20 ml) under a nitrogen atmosphere was added 2-Methylmagnesium chloride in tetrahydrofuran (4.16 ml, 8.32 mmol) and the mixture was heated at reflux for one hour. To the warm reaction mixture was added methyl 5-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (0.89 g, 3.96 mmol) in tetrahydrofuran (10 ml) and the resulting mixture was heated overnight. Then the reaction was cooled to room temperature and the solvent was evaporated. The residue was taken up in ethyl acetate and washed four times with 0.5 N hydrochloric acid. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel; gradient of heptane to heptane/ethyl acetate 1/1) to give 5-chloro-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (1.47 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customTo the warm reaction mixture
  4. temperaturethe resulting mixture was heated overnight
  5. customthe solvent was evaporated
  6. washwashed four times with 0.5 N hydrochloric acid
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (silica gel; gradient of heptane to heptane/ethyl acetate 1/1)

출처 및 근거

ORD 기록
ord-d12add20efa84510ba6caae761c20a6b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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